Acetone → Isopropyl-(6-methoxy-pyridin-3-yl)-amine

HRID 900117Notes

Reaction equation

HRID 900117 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[CH3:10][C:11]([CH3:13])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH:11]([NH:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)([CH3:13])[CH3:10]

Participants

6

Reactant 3

HCID 180AcetoneHCID 811216-Methoxy-3-pyridinylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 28422728Isopropyl-(6-methoxy-pyridin-3-yl)-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-amino-2-methoxypyridine (747 mg, 6.02 mmol) in CH2Cl2 (50 mL) was added acetone (500 μL) and sodium triacetoxyborohydride (1.95 g, 9.20 mmol). The reaction was stirred at room temperature for 20 hours and was diluted with aqueous NaHCO3. The aqueous solution was washed with CH2Cl2 (3×) and the combined organic solutions were washed with brine (1×), dried (MgSO4), filtered and concentrated. The residue was purified by medium pressure chromatography eluting with a solvent gradient (5% EtOAc in hexanes to 50% EtOAc in hexanes) to provide 810 mg of isopropyl-(6-methoxy-pyridin-3-yl)-amine. 1H NMR (CDCl3) δ 7.55 (s, 1H), 6.96 (dd, 1H), 6.61 (d, 1H), 3.86 (s, 3H), 3.52 (m, 1H), 1.19 (d, 6H).

Workup

  1. washThe aqueous solution was washed with CH2Cl2 (3×)
  2. washthe combined organic solutions were washed with brine (1×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by medium pressure chromatography
  7. washeluting with a solvent gradient (5% EtOAc in hexanes to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f89b1bca5e064e76befab16e507edcdc
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

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